


Daring

by RavenDark



Category: Gilmore Girls
Genre: F/M
Language: English
Status: Completed
Published: 2016-09-02
Updated: 2016-09-02
Packaged: 2018-08-12 12:17:22
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 11,467
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7934311
Author URL: https://archiveofourown.org/users/RavenDark/pseuds/RavenDark
Summary: <blockquote class="userstuff">
              <p>TRORY FanFic Challenge Submission<br/>Things to Include:<br/>1. Plot line based on the French film "Love Me If You Dare" - General gist:  Two kids, a girl and a guy start playing this game of daring each other, over the course of time the dares become meaner and meaner as the two try to hurt each other because of what they feel for each other.  Eventually after a dare goes terribly wrong, one dares the other for space…<br/>2. Rory's dares have to get increasingly meaner, as does she, and eventually Tristan is the one to make the dare that they don't see each other for five years.<br/>3. Tristan is a bit of a bastard, but it's his nature and not something he puts on.<br/>4. Rory makes the first move Tristan, and is the first to fall for him (you know, basically Rory chasing Tristan).</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> After writing the Summer Fic Challenge "Sore Winners" and having it be well received by those around me I was feeling euphoric so I jumped at the next fic challenge I could find. Getting *THIS* challenge was sobering (LOL.) A friend ended up buying me the movie and sitting with me so we could watch it and try to work out ideas for a Gilmore Girls story line that would work. Honestly, I thought I would have to give up on it.
> 
> In the end, I had a blast writing it, the idea to interweave this fic into the first season of the series worked well for me. The story ended up being a labor of love and I was actually a little sad to when I got close to the end. 
> 
> Because it was a Fic Submission, it was posted all in one shot, so I will do the same here. I would love some feedback though. Did the story work for you? Do you think I was able to check off all of the "things to include" in the request while keeping the characters believable? Drop me a line and let me know.

****Part 1****

"Excuse me!" Rory stomped her foot in frustration, "I need my book back."

"Say please…" The blonde held the paperback away from the fiery brunette.

Rory exhaled loudly, "Please…"

"Oh that was way too easy," the blonde smiled a taunting leer, "how about a kiss for the book? Name's Tristan by the way…"

"Tristan?" Rory walked up to him with pouty frown. Her wide eyes sparkled with innocence, her hair cascaded down her shoulders making Tristan think of a milk-chocolate waterfall. Her lips were parted and had the sheen of bubblegum lipgloss. Tristan had to admit that he was impressed; she had met his gaze and walked right up to him without blushing or looking away. Was it possible that she really couldn't read the look in his eyes? Was she _that_ innocent? Tristan leaned down a little to see how far this little girl was willing to play the game but instead was surprised by a double-fist to the gut which sent him back coughing for air dropping the book in the process.

"Jerk." Rory huffed out as she picked up her book and walked away, "I dare you to try that again!"

Tristan, floor-bound, could only chuckle in appreciation of the fine looking ass stomping away from him. She had a bit of a Paris thing going for her, "I'll see you around, Mary!"

****End of Part 1****


	2. Chapter 2

****Part 2****

"pst… pst…"

Rory looked up from her paper to see what the person in front of her wanted. The boy, whom Rory had not had the pleasure of meeting yet pretended to rest his head on his hand as he held a folded piece of paper to her. Rory looked around to make sure nobody was watching her before she palmed the note, when nobody around was looking she opened the note,

_-I got 7.42 for question 9. What did you get, Mary?_

Rory looked up annoyed to see Tristan flashing her a sexy smug smile. Rory looked around to make sure the teacher was still lost behind the sports section of the paper before furiously scribbling,

_-We are in ENGLISH CLASS Tristan… Essay questions?!_

It wasn't long before another note came her way

_-Thank you, I knew I could count on you. Thanks for the peep show by the way, Mary._

Rory looked up at slamming her legs together; she was wearing her leggings, but still… Tristan's eyes were full of laughter. Rory wasn't so amused.

_-Don't call me Mary_

_-If the name fits… Mary._

_-I am not a Mary_

_-Mary please… who are you kidding?_

_-I am not a Mary!_

_-Prove it then._

"What?!" Rory said out loud surprising herself. A couple of her classmates hushed her.

"Silence" The teacher called from behind his paper but did not look up. Tristan allowed himself a chuckle before taking out another sheet of paper.

_-Prove that you are not a Mary, Mary. Do something naughty. The books on your desk… drop them on the floor… Make Professor McKenzie jump._

Tristan folded the paper before casually passing it to a very irritated Paris who snatched it angrily away from him and slammed it down on Madeline's desk.

"You're so lucky!" Madeline whispered to Rory handing her the note. Rory opened it hastily then looked up meeting Tristan's eyes,

"No way!" she mouthed at him smoothing down the paper so she could write a scathing response but noticed Tristan's lips were moving. His eyes sparkled; his message was easy to read,

" _I dare you…_ "

"You're crazy!" Rory whispered a little loudly.

"Shhh!" Paris scolded her, jealousy oozing out of every pore. Tristan shrugged his shoulders holding up his hands,

"fine…"

Tristan turned forward to see the teacher then turned back to Rory making sign-language letters at her. Rory did not know sign-language, but she didn't have to know to understand the letters he was signing to her,

"M – A – R – Y"

Rory clenched her jaw feeling her blood boil. She wanted nothing more than to wipe that iridescent, smug smile from his face. She also wanted to punch Paris's condescending look away from her, but Tristan came first. Rory looked up at the teacher and then looked around to make nobody was looking her way. Feeling cold, nervous, and excited at the same time she slowly nudged her books to the edge of her desk. Rory looked around one more time for safe measure and focused on the back of Tristan's head as she gave the stack of books a final bump that sent them off the desk. As if in slow motion, the books tumbled down, the first book to hit the floor, a large fat textbook, slammed flat on the tile floor in a thunderous roar that made every student jump and shriek in their seats and caused Professor McKenzie to holler "What the fuck?!" as he nearly fell off his chair. The other books that followed fell on top of the first and scattered out all over the floor. When the ruckus quieted down, all eyes were on her.

"Ms. Gilmore. What part of _all books away_ at the beginning of class did you fail to understand?" McKenzie snarled.

"Umm… I'm sorry professor Mc-"

"That will be a twenty point deduction off your score. I hope for your sake that your paper is in top form Ms. Gilmore… a failing grade is not a good way to start your education here."

From the corner of her eye, Rory could tell that Paris was grinning like an idiot.

"Shut up!" Rory hissed at her as she retrieved her books from the floor. She was fairly certain the teacher would not hear.

"…and that will be a detention after school Ms. Gilmore, you will write a thousand word essay on first impressions for me; splendid way to make yours by the way… splendid."

"Sorry" Rory gritted forcing herself to settle down.

_Stupid Tristan_

Rory put her books under her desk. Four books, she was missing one. She looked around but did not see it. Then, instinctively she looked towards the front of the class where Tristan smiled at her, book in hand.

****End of Part 2****

  


 


	3. Chapter 3

****Part 3****

"Not bad Rory…" Tristan came into the classroom in an effortless stride. Rory, who was in her nine hundred, seventeenth word of her essay looked up venomously. Tristan met her eyes, fire with fire, liking what he saw. He had stood out in the hallway until he saw Professor McKenzie leave the room, in front of Rory, he dug into his blazer pocket and handed Rory back her book, "You dared, so I took… I must admit though, I wasn't expecting you to match so well…"

"Mr. McKenzie will be back soon" Rory tried to ignore him hoping he would just disappear.

"Then we should hurry" Tristan whispered leaning down on her desk.

"What are you, seven?"

"…but with the motor skills of 11… and the sexual prowess of… well, it would be much more interesting if you found out for yourself."

Rory's day had not gone well. Her patience was paper thin… and as sexy as this guy was… she was not in the mood for any of this,

"Piss off Tristan"

"Off where?"

"That window for all I care…" Rory hadn't really followed the conversation there, but she was hoping to end it with that.

"You don't think I would do it do you?

"I don't think much of you at all…"

"Is that a dare, Rory?"

"Yes" Rory rolled her eyes not really paying attention, "a dare!"

"Cool…" Tristan walked away from Rory who sighed relieved, "you're on"

Out in the hallway, Louise stopped in her tracks when she spotted what looked like Tristan going for his fly as he walked away to the open window in the corner away from her.

"Oh my…" Louise breathed out. It could have been her overzealous imagination, but she swore she was getting a peek at a very impressive silhouette.

"Mr. Dugray! What do you think you are doing?!"

"See ya…" Louise disappeared regretting not having have gotten a better look, but she had gossip to spread and she couldn't do that if she was in detention too.

"Mr. Dugray, explain yourself!"

Rory didn't know what was going on… she didn't want to know what was going on, she just tried to ignore the ruckus while she scribbled away… nine hundred seventy-eight… nine hundred seventy-nine…

"I was thinking that the bushes could use some watering"

"Is this how it is going to be Tristan… You are going to, literally, _piss_ your life away?"

Rory's head snapped up wide-eyed. A chuckle escaped her lips.

The teacher noticed, "I don't suppose _you_ had something to do with this?!"

"Umm…what? No… No!"

"Are you done with your essay?"

She was

"I am." Rory held out her paper.

"Go then," Professor McKenzie ran his hand through his thinning hair, "Take this one with you. School's over… he's society's problem now."

Tristan grabbed her book back from her desk pocketing it with a wink as he walked to the door holding it open for her,

"Shall we?"

Rory grabbed her big yellow book bag and walked out not bothering to wait for Tristan who watched her leave, turned to see Professor McKenzie's tired face, and then followed her out staying a step behind her. They silently made their way to the stairway until Rory's curiosity got the better of her,

"Did you really… you know, water the bushes?"

"You dared" Tristan answered simply, not even bothering to slow his pace. Rory had to widen her next couple of steps to ask her next question making Tristan smile.

"Is everything a game to you?"

"Just the parts worth playing…"

"So if I dared you to leave me alone?"

"Nopes… Sorry… I am two to your one… The next dare is mine"

"You can't be serious" Rory furrowed her brow but kept on walking.

"You make it what it is…" Tristan shrugged his shoulders blameless, "but games have rules. Rory"

Rory had to admit, as much as this guy had gotten on her nerves, he had peaked her interest, "and if I don't want to play?"

" _Everybody_ wants to play. It's the point when you decide to quit playing that says worlds about you as a person though.

Rory let those words sink into her head… He sort of almost made sense…

"So when do you quit?"

"When the value of me not playing exceeds the value of the game" Tristan leaned on the wall half blocking her path.

"You mean when someone makes it worth your while" Rory clarified as she pushed Tristan to start walking down the steps,

"Something like that"

"Okay then," Rory's face brimmed with determination, "What's my dare?"

Tristan stopped in his tracks to see Rory facing him in challenge; she stood a couple of steps below a window, the light cast an angelic-looking halo all around her. Tristan smiled mischievously,

"You see that window behind you?... Moon it"

"What?! You're nuts!"

"That's the dare… take it or leave"

"Leave it!" Rory did not give the option a second thought.

"So be it…" Tristan put his hands in his pockets and continued walking downstairs. Rory looked on,

"Don't I get another dare?"

"Nopes…" Tristan called out loudly, "you only get the one..."

Rory pressed her lips together thoughtfully as she heard the doors slam shut.

****End of Part 3****

 


	4. Chapter 4

****Part 4****

Tristan's dare danced in her head all the way home. Lorelai had tried to make conversation but the only things she heard was _"It's the point when you quit playing that says worlds about you…"_

Before Rory had gotten in the jeep, she had looked up at _the window_ , it was pretty high up. She herself had not realized there _was_ a window there.

All the way home, all through dinner, all through her shower and her mountain of homework she thought about _the point_ where she had _called it quits…_

It was a stupid game. Made up by a stupid kid.

But there she was, thinking things through.

The following day Rory found Tristan at the center of a lunchtime gossip circle.

"Hey!" the throng called out in complaint as Rory yanked Tristan away by the lapel of his jacket.

"Don't worry girls!" someone called out from the circle as Tristan held his hands up in feigned innocence, "I am sure there will be enough left to go around when he gets back!"

Rory turned a hot shade of red but couldn't help being amused. Roughly, she pushed him into the stairway.

"How can we lock this door?" Rory asked him quickly before she lost her nerve. Tristan smiled, he pushed his head out and spoke to a sophomore walking nearby,

"Hey kid… I need you to run interference for me"

"For how long" the kid answered after looking around to make sure _he_ was being spoken to.

"Until I relive you of your post, freshman"

"I'm a soph… okay, fine" the kid walked over to the door. Tristan closed the door.

"Done"

Rory watched him not amused

"Give me your belt"

"Yeah?" Tristan's smile lustfully

"Just give me you're your belt"

"You know, your lack of trust is disheartening…" Tristan removed his belt handing it to her. Rory looped it around the push handles locking them shut.

"What if there is a fire?" Tristan teased

"Then it will be _your_ belt that killed tons of annoying spoiled rich kids… Get the downstairs door."

Tristan could almost feel Rory's heart racing in anticipation… the adrenaline in her body steamed off her pores.

"I don't have another be-" He smirked looking up. Rory's hands were underneath her skirt as she tried to wiggle out of her leggings. Tristan noticed that her shoes were next to her yellow book bag, which lay open against the wall. His breath caught in his throat, the word "belt" came out a rasped gasp. Rory looked up to see Tristan's gaze directly on her.

"Go stand by the door" she said feeling a blush start at her feet and travel up her body. Especially when she noticed Tristan lick his lips as he turned the corner.

The anxiety was killing her. The pressure in her chest was surreal, her breasts ached something fierce as she stepped out of her leggings. She heard Tristan utter a stifled groan from downstairs and she knew she had just flashed him a good amount of naked thigh which mortified her but did not stop her. The floor was cold against her feet and the new sensation almost caused her to call the whole thing off.

Almost

Tristan shook off the initial shock of turning his head to just the right place at just the right time to see Rory lifting her leg as she stepped out of her leggings and focused on the immediate next step. _Memorizing_ , the sight of Rory lifting her leg as she stepped out of her leggings. Those baby smooth pale legs that seemed to go on forever… Those dainty toenails which he swore were painted red… His mouth watered. The promise of seeing her do what she apparently had set herself to do was intoxicating. Tristan pulled the two doors closed with a loud clang which was followed by the bone-chilling hollering of scores of students coming from the other side of the stone stairway. Tristan snapped his neck to see Rory step away from the window pale and wide-eyed.

"Oh my God!" she swallowed hard.

"You didn't wait for me" Tristan pouted surprised

"That wasn't part of the dare!" her voice came out high pitched and scared

"You didn't wait for me" Tristan clearly pouted this time

" _I think it's this one!_ " someone shouted from behind the doors Tristan was holding.

"Go" Tristan advised tightening his grip on the doors

"Oh my God!" Rory panicked.

Someone pulled at the doors

"Go!" Tristan pulled them closed.

" _Yeah it's this one!_ " another voice

"What about the book?!" Rory clutched her shoes to her chest

"Catch!" Tristan tossed one handed as he appealed to Rory's better reasoning which had the desired effect, Rory turned on her heels to climb back up to the other door. As she did so, her skirt flared out giving Tristan another peek at Rory's naked legs. His stomach twitched at the sight,

"Rory quick, what's _my_ dare?!"

"What?!" Rory struggled with the belt upstairs

"My next dare! What is it?!"

"I dunno?!" Rory appeared halfway down the steps again to give him an angry look as she tossed him his belt, "salute the flag pole!"

"That's it?!" Tristan got caught looking up Rory's skirt. He didn't blush or act embarrassed. He met her eyes and winked. Rory felt her body go hot for the umpteenth time; she bit her bottom lip as she picked up her book bag again and rushed upstairs.

"In your underwear!" She called out as she pulled the door open harshly startling the sophomore keeping guard,

"Thanks, you're services are no longer needed"

The sophomore looked inside the stairway to see Tristan walking up the steps casually closing his belt. He had a smug smile on his face, and there appeared to be some kind of commotion at the bottom.

****End of Part 4****


	5. Chapter 5

****Part 5****

Rory couldn't believe that she had done that! Her heart was racing and a warm wave whooshed throughout her body. It felt nice. No, it felt wonderful! That had been a stupid thing to do… she could have gotten in a lot of trouble had she been caught… but she hadn't. She had gotten away with it, and the adrenaline rush was incredible! Her body felt alive, her extremities tingled in a way that made her blush.

The rest of the school day was a daze. She couldn't concentrate; Mr. Medina had to call her name twice in class to get her attention. She had blushed hard the last time as all eyes fell on her, but it really didn't matter. She was proud of pulling off that little stunt. If people knew it had been her… Well, nobody would be able to call her "Mary" anymore then could they?

"Ms. Gilmore!"

Rory snapped out of her reverie.

"Sorry" Rory mumbled sitting up straight on her chair, but her mind was already wondering again…

The next day Rory continued to relive the event in her mind as she made it to school; there was a big crowd at the entrance.

Something was going down.

"What's going on?" Rory cautiously asked towards the group of girls nearest her, Madeline and Louise. It was Paris though, not far from them who spoke up first,

"Some imbecile decided it'd be cute to greet the student body wearing nothing but a paper bag over his head."

"He was naked?" Rory raised her eyebrows clueless.

"No…" Madeline pouted, "He was wearing boxers… and I think he was saluting the flag when he got picked up"

Rory's stomach fell.

"No!"

"Dumbass" Paris sneered

"I think it was Tristan…" Louise drawled lazily

"Tristan. Be serious" Paris berated

"I _am_ serious…" Louise lowered her eyelids for emphasis, "I think I _recognized_ something…"

"Really…?" Madeline's lips curled mischievously

"You two are worthless, you know that?" Paris admonished

"What happened to Tri… the guy?" Rory asked softly

"Charleston's office. Poor shmuck is probably looking at an expulsion for this. As if we needed another society comeback in a couple of years"

"How are the Jameson twins?" Madeline asked

"I heard the rehab center they were crashing in Manhattan kicked them out for dealing during group therapy" Louise started, "Supposedly…"

Rory walked away then feeling like the gum currently stuck under her shoe. Worse even, the dirt that was stuck on the gum stuck under her shoe. That is what she felt as, gum dirt.

It _had_ been Tristan of course; something the entire school body learned when he failed to show for his classes two days in a row. By the third the whole school was buzzing eagerly anticipating the return of their new hero. On the fourth, Tristan gave them just that, a hero's return at the completion of his short suspension. He was on his way to becoming bigger than any of the other Dugrays that had walked the halls of Chilton.

"What do you want to be?" Rory asked him one day in the library as he carelessly shuffled the cards of the library index.

"Wha?" Tristan raised his brow at her nonchalantly

"When you leave here; you could have gotten into a lot of trouble for what you did!"

"You dared." He flashed Rory a smile.

"Yes but… I never thought you'd do it! Surely you won't be a… What do you want to be when and if you graduate from here?"

"I thought that was obvious…" another smile. Her chest tightened.

"Enlighten me"

"A tyrant"

"Huh?"

Tristan stuffed the cards back in the little wooden drawer and pushed it shut before turning his body to face Rory who blushed and took a step back. She hadn't realized she had been standing so close to him. She could feel the heat radiating from his body, it was making her dizzy.

"Dugrays have always been known for leaving their mark in the world… Dugray men specially are expected to do so, big marks.

Rory unconsciously held her breath, the words coming out of his mouth tickled her insides… when he said "marks" she could feel the period that ended that sentence where _no one_ should feel a punctuation mark… but he wasn't done speaking…

"…to leave the biggest marks of them all… _Everywhere_ I go."

Rory swallowed feeling hot and overdressed. She breathed from her mouth convinced that her nose couldn't supply the amount of air she needed just then.

"Rory…"

Tristan saying her name made her shiver.

"Yeah…?" Rory bit her lip.

"The book?"

Rory met his eyes and took another step back. The book had been her prize for her moment of courage; it had become the symbol of her spontaneity and a secret badge of her determination. She didn't want to give it up.

"What's _my_ next dare?"

Tristan smiled lustfully, it took Rory's breath away.

"You know… I haven't been able to take the image of you showing the entire world your rear end out of my mind… It was very unfair of you not to have waited for me…"

"Tough" Rory frowned not liking where this was going.

"Well yeah" Tristan stepped away from the index catalog easily breaking into stride. Rory caught by surprise had to hustle to catch up with him, "Imagination is a powerful thing… frankly, I don't think you could do what I see here justice…"

Rory pursed her lips as he stifled a laugh touching his forehead. She almost opened her mouth but was able to recognize the out when it was given to her. She came close to breathing a sigh of relief when his next words spilled out of his mouth,

"I want you to flash me…"

"Excuse me?" Rory's face felt hot.

"Here" Tristan explained casually, "for no less than ten seconds..."

"I… I have a boyfriend" Rory blurted

"Then we better not delay this… you never know when he may get the impulse to take the bus ride over and come barging in here ranting!" Tristan emphasized his diatribe by extending his arms, which got them more attention than Rory wanted at that moment.

"Shut up!" she pushed him into a row of bookcases looking around for safe measure, "I can't flash you! The library's full of people!"

"Want me to empty it?" Tristan looked right through Rory at something on the wall. Rory turned around following his gaze to the fire alarm.

"You wouldn't"

"You've got your dare…" Tristan began to walk towards the wall, "I'll help you"

"No!" She grabbed him by the elbow and dragged him to a corner of the library, next to books that had not been taken out of their shelf since they have been placed there eons ago. Rory's face felt hot and her breasts were feeling a familiar tingle. Reaching the spot she had been looking for she swung Tristan against the wall where he smiled at her bravado.

"I'm not taking off my bra" Rory breathed out resolutely. Tristan sighed heavily but leaned against wall compliantly,

"Well, I didn't make that part of the dare… so I guess I can't complain now can I?"

"Five seconds" Rory tested Tristan nervously looking around the corner.

" _I'll_ take it…" Tristan shrugged his shoulders, then scrunched his nose playfully, "but the dare's for ten"

Rory shot him an angry look; she swallowed feeling a warm familiar feeling travel up her body as she pulled her shirt out of her skirt. Her legs felt hot, tingly, she wished she hadn't been wearing her leggings… she felt all clammy and squirmy in them all of a sudden. She felt numb, her fingers in paticular, so she had to concentrate on each button that she had to undo. The first one was easy… the next one exposed her bellybutton and was much harder to undo. Tristan inhaled sharply at the sight of her pale soft skin, the next button undone showed him that while Rory wasn't doing crunches every night… her stomach was still flat and toned enough to make his mouth water.

Rory's fingers trembled a little with the next button and she had to fight with herself to go through with it. She could feel Tristan's gaze on her burning her image into his memory… she loved the way that felt. She wished she had been wearing a padded bra so that her arousal wouldn't be so evident… but then again she hadn't been expecting to be standing in front of Tristan holding the sides of her shirt closed as she breathed calming breaths, steadying herself for the last two buttons.

Tristan licked his lips and held his breath as Rory's lavender-colored bra came into sight. He could see the apprehension in her posture as she steeled herself to go through with it. He clenched his jaw fighting the urge to go up to her and help her but… He wanted her to do it. He wanted her to go through the motions of undressing for him… The feeling was intense; his stomach felt empty, his boxer briefs tight around his thighs.

"Rory…" He encouraged gutturally. Rory met his eyes feeling weak-kneed and entirely too aroused. Her breasts ached, her nipples strained against the material of her bra… something Tristan would surely take notice off… She took a breath through clenched teeth and made up her mind.

It was now or never.

Rory quickly fumbled with the last two buttons and held the sides of her shirt together as the rush of having just gone through that washed over her. When the feeling faded slightly, she looked up and met Tristan's darkened blue eyes,

"Ready?" Rory shot Tristan a fiery look.

Tristan nodded dry mouthed. Rory swallowed, but still felt as if she were drowning,

"Ten seconds?"

Tristan nodded again holding up his hands in loose fists. Almost shaking, Rory looked around the corner again to make sure they were still alone and opened her shirt letting it fall off her shoulders making her feel monumentally more exposed. She tightened her jaw as she tried to meet his gaze unsuccessfully… his eyes were focused lower on her body

_God… It's not as if I were completely naked..._

_Damn_ , Tristan couldn't tear his gaze away; _she might as well be naked…_

Slowly, Tristan opened up fingers keeping count…

_Two…_

_Three…_

Rory shivered, and goose bumps appeared on her stomach and the top swells of her breasts.

_Four…_

Her bra was very thin, thin enough that he could trace the outline of her nipples with his eyes clearly distinguishing their slightly darker hue…

_Five…_

Rory gasped feeling more exposed with each passing second. Her palms felt clammy.

_Six…_

She gripped the sides of her shirt and almost closed the shirt around her, but stopped herself as her knuckles brushed against her stomach and she jolted herself aware again.

At the count of _seven_ both heard footsteps approaching, Rory's eyes widened in panic, Tristan's smile turned into a full-fledged leer. He locked eyes with her to keep her from running away now that she was so close to finishing her dare.

"Tristan!" Rory begged at the count of _eight_. She stomped her foot in frustration but kept the sides of her shirt open. Tristan was not going to let her out of this, the warning look in his eyes told her that much.

_Nine…_

There was no way Tristan was going to let her off the hook. The footsteps grew louder, closer; Rory was shaking, practically trying to writhe out of her skin making her breasts bounce delightfully. She squeezed her thighs together and her pixie face contorted as if she were going to cry.

_Ten…_

Rory slammed her hands together closing her shirt and bolted into the nearest row of books though not before shooting Tristan a hateful look. She'd get him back for that...

"Oh! There really _is_ someone back here!" Rory heard the soft voice of Mrs. Jackson, the librarian, "what is your name young man?"

"Dugray ma'am… Tristan D"

Rory had to smile as she struggled to put herself to rights. She couldn't imagine herself answering with the composure he held.

"Well Mr. Tristan, you almost got locked inside here by yourself! I almost never make it this far in… Is someone else here?"

Rory held her breath

"Just me… though I think I saw some kids over at the other end"

Rory stifled a laugh.

"Oh my…well you get going now, you don't want to stay here by yourself all night!"

"No ma'am…"

When the footsteps faded, Rory stepped out holding the paperback in her hand.

"Mine"

"Yours…" Tristan smiled tauntingly… Rory was pissed off, that much was obvious. Though he wasn't sure if she was mad because he had made her reach her goal in spite of interruptions… or maybe, because she had failed to reach another…

"Stay" Rory blurted firmly

"Was I going someplace?" Tristan smirked leaning in to breathe the air directly around her. Sweet, with a hint of Tabasco

"Stay here. That's my dare"

"All night" It wasn't a question, Tristan just wanted to make sure Rory understood what she was daring him into.

"All night" Rory repeated resolutely

"Okay" Tristan muttered almost under his breath…

"Tomorrow then" Rory said with the barest hints of emotion. His crystal blue eyes seemed to struggle with something, her body fought against her will to react to it.

"Rory?" Tristan said softly. Her chest tightened, she looked into his eyes expectantly. Tristan smirked,

"Nice bra"

Rory's face turned red, but not out of embarrassment. She shot him an evil look and pushed back any guilt that she may have had for her dare before she turned around and marched out the library… _Jerk_.

  
****End of Part 5****

 

**Notes for the Chapter:**

> A/N - The "tyrant" reference in the library was a tie-in to the movie this challenge refers to. In the movie "Love Me if you Dare" (Jeux d'enfants) the young girl, Sophie accuses the boy, Julien of wanting to be a tyrant over her, something she references again later in the movie. I put a spin on it ;-)


	6. Chapter 6

****Part 6****

Rory couldn't help it though, she felt guilty. She had already gotten him suspended once, if Tristan actually decided to go through with her dare.

 _Well he can't be that stupid_ she thought as she practically ran through the halls the next morning. The library was closed, it was five minutes to the beginning of class and the library was locked. That was not a good sign. She felt a chill travel down her spine and a wave of panic threatened to wash over her.

"Paris?!" Rory called out when she spotted her about to climb the stairs to the second floor, "wha… what happened here?"

Paris narrowed her eyes maliciously at Rory before turning the corner. She had no way of knowing that Tristan's prank had been of Rory's doing, but she very much resented the fact that Rory seemed to be obviously expecting him there. Rory bit back the urge to yell something at Paris, she looked around desperate for someone who could answer her questions, but finding nobody she had to resign herself to her first class and the idea that maybe, he was _that stupid_ …

Tristan's suspension had lasted ten days this time around. Few people wondered what had come up with him, most just waited to see what he would do next. It was bound to get him expelled.

Rory felt horrible, she had tried to call his house when he didn't collect the book from her in days but she never got past the sixth digit before hanging up frustrated with herself. Much as in her dare, with each passing day she felt something building inside her. A pressure that was not exclusively concern, she couldn't identify it, but it was building stronger and stronger inside her. She could almost say it was anxiety, but was embarrassed to do so; she thought of her last two dares and couldn't help but be curious as to what he would ask her to do next.

Okay not just curious, she was dying to know, she needed to know; it was all she thought about. It made her stomach tingle and her ears burn.

So of course when he came back, he let her stew.

He waited a week before he walked up behind her and casually picked up the book from the table where she ate. He waited until her mouth was full before he did so, Rory could only look up as Tristan's sapphire blue eyes focused on hers with warning. Rory could not keep their eye contact together for long and clandestinely looked around the room to see if anybody had noticed their perverse exchange of glances. When she looked back his way she found him still smiling, nonchalantly pocketing the book in his navy blazer.

Tristan let Rory squirm for another week before she got her next dare. Every time he walked by her, Rory's anxiety rose just to be deflated when he'd continue walking past her without as much as a half-assed attempt at picking her up. It would have been easy to assume that the game was over, that he had grown tired of it, of her. Except that his forewarning, hell-sent looks were crystal clear, the game was far from over… he was just taking his time. In the process, he was driving Rory crazy.

Rory _was_ going crazy. The anticipation was exhausting, her next dare was almost the only thing she could think about, and it was having a toll in her life. She was constantly distracted. Her school teachers had noticed, her mother had noticed, worse of all Dean had noticed. She hadn't been responding to him as she had before, she could see it in his face that he was bothered by it and was frustrated that he seemed too dense to figure out what to do about it.

"Do you want it?" Rory felt breathed in her ear one day out of the blue

"Oh!" Rory gasped leaping out of her skin. She had thought the school empty long ago, "You scared me!"

Tristan answered her with a smile that made her breath catch in her throat.

_He wouldn't dare her now, there was no one there… where was the excitement in that?!_

"I dare you…" Tristan slithered

_Shit_

"…to kiss me"

"What?!" Rory's eyes shot to his, feeling the color drain from her face.

"Kiss me"

"I… I… I have a Dean" Rory blurted feeling her feet go cold, "remember?"

"and?"

"and… and… he's my boyfriend" Rory tried unconvincingly

"I fail to see the problem" Tristan closed in on Rory. Her chest rose and fell in tiny bursts. Her eyes held fear and trepidation behind them.

"I… can't" Rory felt her heart pounding in her chest.

"You can't?"

"No" She put her palms on his chest pushing him back, "I can't"

Tristan smile faded some as Rory shrank into herself to side-step him. She first took a timid step forward, then another before breaking into a run that took her away from Tristan, away from her doing something she had thought about doing once too many times.

****End of Part 6****

  


 


	7. Chapter 7

****Part 7****

Rory felt horrible, she had broken up with Dean. Well, _he_ had broken up with _her_ not more than 24 hours ago and she was trying to accomplish a record setting bounce-back at Madeline's party without much success. She wasn't in her element, and she would have left long ago had Lane not met a nice looking Korean boy there.

"Hey am I sick yet?" Rory asked Lane as she passed by her friend who danced with her Korean boy.

"Not yet." Lane crossed her fingers and toes that Rory wouldn't want to leave just yet, "It actually might just be allergies"

"Keep me posted" Rory read her message and took her leave of the couple bumping into Paris almost right away.

"My watched stopped, what time is it?"

"It's 10:35"

"Yes, bye." Paris shoved her way out leaving Rory whip lashed and once again alone. Rory found a quiet spot in the house and pulled out a bit of reading to pass the time… until the sounds of Tristan's current girlfriend reached her ears,

"No. I'm sick of fighting with you. I'm sick of hearing 20 times a day _You're my girlfriend_ "

"Ok could we possibly do this somewhere were a roomful of people aren't staring at us?" Tristan tried to hush his girlfriend.

"I think we should break up"

Rory's breath caught in her throat. She didn't think it was right to be listening in… but she couldn't help herself.

"Ok," Tristan tried, "I really want to go outside and talk about this.

"Then go, bye."

"Summer come on!" Tristan tried again but became self-conscious that he was being watched. He turned in time to see Rory try to dodge his stare. His face burned with embarrassment and self-hatred, he noticed Rory open her mouth to say something to him but he left the room before she could get a word in.

Rory felt as if she should go after him, she felt something in her stomach that told her to get up and follow, but Lane chose at that moment to find her,

"I have a major problem"

"What?" Rory asked distracted, she tried to listen to her friend and keep an eye out for Tristan.

"Henry, the guy I've been dancing with…?"

 

**Notes for the Chapter:**

> **End of Part 7**
> 
> A/N - So this was taken right out of the party episode to setup the next chapter. So go on straight to part 8...


	8. Chapter 8

****Part 8****

"I'm sorry" Rory found Tristan in Madeline's piano room a little bit later.

"About what?"

"About you and Summer" Rory said softly

"I don't want to talk about Summer"

"Ok." Rory thought fast, "How'd you do on that biology test?

"What?"

"The test. It was hard wasn't it?"

"Yeah it was hard" Tristan answered not really paying attention.

"I got a B plus"

"What are you doing?"

"Talking about the test" Rory feigned ignorance

"Why?"

"Because you said you didn't want to talk about Summer"

"I don't" He bit out

"Ok," Rory's heartbeat sped up a little, "so I moved to biology. Sorry did you want to talk about Spanish?"

"You just loved it, didn't you?"

"Loved what?"

"Seeing me get nailed like that. Must have been a great moment"

"Not really" Rory stammered

"Please" Tristan snapped snidely, "You loved it, she loved it, everybody loved it"

"I did not love it" Rory empathized honestly

"I really liked her too"

Rory hadn't expected that answer, Tristan admitting something like that... Truth be told, it made her feel a little less special, but she didn't stop to think why that was. She answered what she thought he would want to hear,

"Yeah I know"

"So where's your boyfriend tonight?"

"He's..." Rory took a deep breath, "not my boyfriend anymore"

"Why not?"

"He didn't want to be"

"Idiot…" Tristan said simply in that nonchalant way of his, it made Rory want to smile

"So's Summer"

Tristan nodded

"You think you'll get back together?" Tristan asked.

"He was pretty set in his decision" Rory confided heavy hearted.

"When did it happen?"

"Yesterday"

"Wow" Tristan could not think of something comforting to say.

"It was our three month anniversary" Rory admitted.

"That sucks" His vocabulary failed him still.

"Yeah it does suck. Do you think you guys will?"

"No, no" Tristan thought back to the embarrassment that damned girl had just put him through, "No, no, no, no, no"

"So no?"

"No. Hey, I'm sorry I gave you such a hard time for a while"

"Oh that's ok" Rory dismissed automatically

"It is?"

"Well no, but you're sad"

"Yeah well. I am sorry" He looked at Rory's profile thinking of the dare she did not follow through with.

"I accept your apology"

"Oh man," he felt hot again, "it's a great party huh?"

"Yeah not bad. It gave me a chance to catch up on my reading" Rory held up her book. Tristan wanted to chuckle,

"You are very odd, you know that?"

"Thank you" Rory thought of the dare she had refused earlier, it didn't seem so daunting now.

"You're welcome," Tristan nodded turning to her. Rory was close to him; he could feel her heat like he could feel the anticipation in his chest but he did not lean in to kiss her until he felt her lean in first. The kiss was hers to initiate, the paperback in his pocket told him so. Her lips were soft, the kiss dream-like, a kiss that wasn't awkward or impulsive… that is until she pulled away with tears in her eyes,

"I'm sorry, what did I do? Did I bite your lip or something?"

"No it's not you." The kiss felt entirely too _not wrong_ , "It's just - I have to go"

Tristan looked on as Rory fled.

"We have to go" Rory found Lane.

"Rory are you ok?" Lane turned to Henry, "I have to go."

"Well wait," Henry called out to Lane, "can I get your number?"

"Last name's Kim and we're the only ones in Stars Hollow!" Kim replied excitedly then grabbed Rory's arm tightly, "I can't believe I just gave my number to a potential Korean doctor..."

****End of Part 8****

 


	9. Chapter 9

****Part 9****

Though it had been an awkward morning, Rory collected the paperback from Tristan the next day, and sooner than later had reconciled with Dean not forgetting the kiss she had shared with Tristan that night at Madeline's. The kiss with Tristan stayed on her lips long after that party and dwelled on her memories with every smirk and smart comment of that smug face of his. She tried to replace the angered yen she found herself feeling for Tristan into passion and faithfulness for Dean, her boyfriend, but at the end of the day she still found herself wanting.

"Kiss me"

"Rory?" Tristan doubled back not sure if he had understood. They had been rehearsing a scene from Romeo and Juliet for school in Miss Patty's studio for days. At the end of each day, both had looked for things to keep them in the studio after everybody had gone, but Dean had found a way to get out of work before the last person left every night.

Dean was nowhere in sight that night however, Rory looked nervous but nonetheless determined, a look that drove Tristan crazy.

"I dare you" Rory stood before him, book in hand.

Tristan did not need to be told twice.

Tristan pinned Rory to the shelf of props behind her with his body. He heard her utter a half cry before his lips crashed on top of hers. Her body felt feverish, her lips hungry… Tristan began to undo the buttons of her shirt amazed that she didn't try to stop him. He had almost reached the last button when a loud booming noise made them pull away. They listened, frozen in place to the sound of tumblers falling in place.

"I think Miss Patty locked us in…" Rory's chest heaved.

"I see…" Tristan walked a bit towards the door to see if there was any other late straggler yet to leave. There wasn't.

They hadn't been alone, but they were alone now. The pause that followed as that reality sunk into both their brains was an awkward one.

Rory wanted to continue where they had left off, but now Tristan stood several yards away from her. If she went up to him… well… she still had a boyfriend, and the moment seemed to be fading fast. She took a gamble.

Tristan turned around to see Rory's halfway open shirt, stay halfway open. It was almost eight pm, the sun had fallen long ago and the moonlight shone through the window casting an eerie glow on Rory's exposed skin. The sight of her smooth stomach and beginnings of a light-colored bra made Tristan's skin tingle.

The moment was over Tristan reasoned sadly, Rory had a boyfriend and much as that didn't bother him one bit, he was sure it would stop Rory dead in her tracks.

Tristan watched Rory stand near the window, her mouth open… her lips glistening. He noticed her look down at the book in her hand and caught it when she tossed it to him for meeting her dare. It was the invitation he was waiting for. Tristan held the book up, dare for dare,

"Come here…"

She did.

Tristan had inadvertently stepped into the shadows, so Rory couldn't see his eyes which made it much easier for her to finish his work and open up the last buttons of her shirt before she fell into his arms as their lips crashed together.

No matter how much Rory thought of that night afterwards, she would never be able to recall the point when things stopped being about the book or a silly game to her. She had vivid recollections of the entire night, just not of that. Rory's body shivered slightly when Tristan's fingertips touched her bare stomach, tracing their way around her back to pull her closer. Rory didn't remember moving, but she remembered Tristan pulling a mat from a rack in between kisses and laying it down so he could sit her down on it beneath the moonlight shining through an open window. Rory felt a blush creep over her body when his experienced hands undid the snaps of her bra before he pulled back, sat up, and removed his shirt and undershirt together not breaking their eye contact. Understanding that he wanted her do it, Rory timidly followed suit and shrugged off her bra swallowing hard as she moved her arm down so that Tristan could see her.

The kiss that followed wasn't hungry or intense; it was soft, languid, and full of words that had never been spoken. It was a kiss that convinced Rory that there were things outside of Stars Hollow and small markets bagboys. Rory closed her eyes despite wanting to keep them open. The moonlight shone on Tristan's wide shoulders, his hair shone with platinum highlights, his hands were wandered down her body and she decided she didn't want know where they were headed, she wanted to be surprised…

Rory felt a pang of anxiety when she felt Tristan's hands on the sides of her open jeans but lifted her hips nonetheless so he could ease them off her. She wished she had a blanket, a sheet, anything to cover up with, but considering that they were on the floor having rolled off the mat a while ago she knew it was a long shot to ask for one. So she didn't, instead she focused on the floor beneath her. Hardwood floors were never really clean, no matter how well they were swept there always remained something on them, so Rory focused on the grains of sand and dirt that stuck to her back as Tristan swallowed her cries in his mouth as he entered her slowly.

"You okay?" Tristan broke the silence in a throaty whisper. When she didn't reply right away he pulled his head back to look at her but she buried her face in the crook of his neck,

"Give me a sec," she whimpered out as she became adjusted to him. Tristan held his breath and waited for her to nod before he pulled out partially only to enter her again, easier this time.

"Ugh…" Rory coughed out feeling all of Tristan in her, she felt a bead of cold sweat roll down the back of her neck unto the floor. Her skin felt prickly, hot and cold at the same time and most likely in need of a bad shower when they finished.

"Shit…" Tristan grunted to himself as he tangled a dusty hand in Rory's hair to move her face in order to kiss her. She had her arms tightly wrapped around him and she squeezed him with her thighs, it made things difficult for him, but he was up to it. A nuclear bomb could have exploded around them and it would not have stopped Tristan from thrusting in and out of Rory…

"Oh God!" Rory cried feeling her body contracting. She was close, she gasped for breath and dug her nails into Tristan's back. Tristan groaned loudly but did not stop. His breathing was coming in loud open-mouthed grunts and his elbows ached from holding up his weight on the hard floor. His stomach tightened, Rory was just surreal… The scratches on his back stung.

Rory shut her eyes tight, she couldn't see anything anyway, everything had become clouded and fuzzy. Her back was killing her and the air that crept underneath the barn doors was ice-cold making her nipples tighten painfully. Still, her toes curled as everything her ultra-sensitive body felt traveled to the one point that was driving her crazy.

"Come Rory…" she heard Tristan groan

"What?" Rory gasped out. _What did he want? What had he said?_ "…where?"

"Oh Fuck…" Tristan clenched his teeth increasing his pace which pushed Rory over the edge. Rory opened her eyes wide as her orgasm jerked inside her, her body contracted and shook. Tristan felt Rory clamp down on him and exhaled the breath he had been holding loudly as he rode the spasm that overtook him...

"Woah…" Tristan breathed when his heart stopped pounding in his chest, "That was…"

"Yeah…" Rory rolled off from under him to look for her underwear. Tristan noticed that her back was a little dirty and red with many little scratches. He suppressed a chuckle as he pulled up his pants. That was a good look on her.

"I can't find my bra" Rory looked around covering her breasts with one hand while holding her shirt with the other.

"It's by the mat" Tristan pointed as he looked around himself. He walked over a couple of steps and picked up the paperback from the floor. He turned to see Rory buttoning her shirt, he held the book out to her, "here."

Rory looked at the book then at Tristan feeling everything about her go cold,

"Is that the only reason you think I…"

"What?" Tristan furrowed his brow. _What did he do?_

"This is still part of the game to you isn't it?" Rory's chest hurt, as if her heart were physically breaking. She felt two inches tall and shrinking fast.

"I don't understand…" Tristan looked at the brunette in front of him confused.

"Leave"

"Rory"

"Leave!" she snatched the book from Tristan's hands, "Dare's done, my book. Now leave."

"Rory" Tristan tried to meet her eyes but she had none of it

"Please…" she breathed back the sobs that would overtake her the second she was alone, "Just go"

****End of Part 9****

 

**Notes for the Chapter:**

> A/N - Woah! what did you think?! I have to know. This challenge was kicking my butt but it was oh so worth it to get to this scene. My toes still curl visualizing it.


	10. Chapter 10

****Part 10****

"I warned you," Paris growled at Tristan, "I am not going to fail this because of you. I will replace you with Brad in a second.

"Oh, dear God, no" Brad gulped air turning for his water bottle.

"Can we take five?" Louise played with her nails, "I'm in serious need of a tall caramel macchiato…"

"I'd like the grandey…" Madeline added

"You can't _say_ Grande." Paris barked, "Fine. Take five; make it twenty, but somebody better bring me a double espresso!"

Everybody went out in different directions. Rory felt the beginnings of a headache lurking behind her eyes. Behind her she could hear Louise,

"Where is there a Starbucks here?"

Followed by the exasperated sounds of Paris giving someone hell… again… and for the hundredth time. Rory closed her eyes and tried to make everybody disappear. It worked for a moment, but as soon as she opened her eyes all the sounds in the studio blared back to life. Rory brought her thumb and forefinger to her temples and walked backstage, there had to be some aspirin in her book bag.

"Rory…" Tristan appeared from behind the curtain, "it's been days, we need to talk."

"There is nothing for us to talk about," Rory rummaged through her book bag, the paperback lay among her other books, "we were just playing a game. That's all"

"Rory…"

"I am trying to forget it happened," Rory refused to look up, "you should too"

"I can't do that Rory"

"Well you're not trying hard enough"

"Rory"

"No Tristan, It was obvious that _it_ was all about the dare. I took it too far, my fault. I _have_ a boyfriend! It should not have happened. I regret it"

"I don't" Tristan tried to meet her eyes, but she refused to look up.

"You should" Rory pushed back feeling a pout on her lips. Tristan tried to make light of the situation,

"but I don't want a boyfriend…"

"You know," Rory snapped her head to face him, "That is exactly what you need!"

"A boyfriend? I don't know how much of that night you remember but-"

"You need a girlfriend, a new girl to keep you busy and away from me… work on that"

"I don't want to forget"

"Well I need you to!" Rory half-shouted, then looked around nervous to see if anybody had heard her. Dean would be there any minute. She dug into her book bag again frustrated that she could not find anything for her headache. She found the book instead, "I dare you."

"What?" Tristan asked surprised

"I dare you…" Rory repeated firmly, resolutely.

"You want me to sleep with another woman?" Tristan looked on in disbelief

"Yes" Rory answered bluntly

"Who?" Tristan tested; there was no way she had thought this through. Sure enough, her eyes widened a little as they looked away. Then,

 _"What's an apothecary anyway?"_ Madeline's voice reached their ears.

"Her" Rory answered without thinking

"Madeline?"

"She as good as any, right?"

Rory's words were like little jabs at his chest. Eventually, he'd have to push back.

"You don't really want me to do this"

"Is that your way of saying that you can't?" Rory taunted on.

"You'll regret this Rory" Tristan tried to sound thoughtful and caring, but that really wasn't in him. He was upset now, and that is how the words came out.

"Don't you threaten me!" Rory hissed, "This is your game remember? If you are not enough of a _tyrant_ to follow through-"

"This changes things you know" Tristan took a step towards the curtain before he said something out of anger.

"It's meant to" Rory locked her eyes with his to make sure there was no confusing her words.

"Okay…" Tristan nodded, "be prepared to give the book back before opening night… do you want proof?"

"Don't be gross" Rory scrunched her nose

"I'm just playing the game, Mary." Tristan said coldly before he pushed past the curtain leaving Rory to wonder what she had done.

Truth was, Rory never thought he'd go through with it. There was no way he'd be that cold-hearted. The game wasn't that important… surely _she_ was more important than bragging rights.

That night _had_ meant something, hadn't it?

****End of Part 10****


	11. Chapter 11

****Part 11****

"I can't believe you're really here…"

"Yeah…" Tristan absent mindedly played with the picture frames on top of the fireplace. It had been less than a week since that night in Stars Hollow. His mind constantly strayed back to that night. Even there, his mind was on one thing, one person, and the airy brunette with the wide nervous smile was not it.

"Are you hungry? I can have Ames make us a cake; we can pretend it's your birthday…" Madeline looked at him through a veil of lashes, "we can have our own special party…"

_Fuck Rory, she dared_

"Is your room this way?" Tristan began climbing the steps; Madeline nodded nervously chewing on the straw from her drink,

"My parents are out of town" she blurted out walking past him to lead the way, "they are spending some time in Aruba"

"Aruba's fun" Tristan responded almost mechanically, "I prefer the snow for this time of year, give me Aspen any day…"

"Oh my God! I say the same thing!" Madeline opened the door to her room but hesitated at the door.

"Madeline?" Tristan kissed her hard pushing her into her room. She tasted of peach and Captain Morgan rum, "You can tell Ames I like chocolate…"

****End of Part 11****

 

 

**Notes for the Chapter:**

> A/N - Tiny update just to setup the rest of the story. I have gotten requests in the past to flesh this out, so I wrote a short fluff piece fleshing this out for another site... I may revisit it and lengthen it to a proper scene to post here if enough people want to see what happened between Tristan and Madeline...


	12. Chapter 12

****Part 12****

"Here's to my love. Oh true apothecary, thy drugs are quick… Line?" Tristan looked up.

"Thus with a kiss, I die. How hard is that to remember?" Paris's blood boiled.

"Thus with a kiss, I die, right… and then I kiss her, right?"

"Yes. You say 'Thus with a kiss, I die.' Then you kiss her and die. Why are you smiling? You think this is a joke? The performance is tomorrow"

"Wait, tomorrow?" Tristan mocked, "Oh my God. I totally missed it the first 47 times you said it"

"Can we just get through the scene?" Rory's chest felt as if it were going to explode. Tristan had avoided her all week, looked for any opportunity to not be around her in private. She needed to speak with him.

"Fine" Paris snapped, "But yell line once more and you're out"

"Oh true apothecary, thy drugs are quick. Thus with a kiss, I die"

Tristan stopped halfway to kissing Rory

"What?" Paris annoyance was very apparent in her voice

"Well, it's just, with this being our last kiss and all; it makes me think about our first kiss. You know, at the party"

"What?!" Rory's eyes shot open. _He wouldn't be this much of an asshole, where was he going to take that?_ She quickly scanned for Dean.

"Lie down, you're dead" Paris reminded her

"We all are" Louise saw her easy grade slipping away

"You remember the kiss," Tristan answered unfazed, "In Act 1 at the Capulet's masked party?"

"What about it?" Paris clenched her jaw

"Well, I was just trying to think of something that would make this kiss as special as that one"

"Tristan" Rory voiced hoping to stop him

"I thought she could cry" Tristan blurted out, clearly alluding to their first _real_ kiss.

"What?" Rory silently begged him to leave it at that.

"She's dead" Paris fought to contain her disdain, "You're dead, lie down"

"Yeah, but that's the beauty of it. No one would expect her to cry" Tristan snidely added

"I would" Dean, who stood by the curtains answered not at all amused

"You know, funny you should say that…" Tristan straightened up

"I need to take five" Rory shot up feeling her heart in the back of her mouth

"You know what?" Paris had had enough, "Let's all take five. That way you can all cancel whatever plans you had tonight because we are staying here until we get this right"

Rory pushed Tristan off to go to Dean. Brad took out his cell phone.

"Who could you possibly be calling?" Louise asked him raising her brow at him.

"He is un-fucking-believable" Dean hissed as soon as Rory was within earshot

"Dean," Rory breathed, "I really need you to leave"

"What?" Dean's head snapped down to look at his girlfriend

"The play is tomorrow, and it's fifty percent of my grade, and you standing there staring at Tristan down," Rory tried to explain, "it's like a challenge or something"

"Well, I don't like the way he's messing with you"

"I don't like it either but we have to get through this scene and we can't get through the scene with you standing there. So, Dean, please" Rory looked up holding her breath

"Fine" Dean pouted angrily "Call me later"

Rory breathed out relieved as she gave him a quick kiss she hoped Tristan didn't see to send Dean on his way. Tristan of course, had noticed the whole exchange, he walked towards Rory,

"Now I noticed you didn't cry when you kissed him. I'm starting to feel a little insecure"

"What is wrong with you?" Rory snapped at him

"Whoa, I think I liked you better comatose"

"I thought you weren't going to say anything" Rory's blood sped up, but really not out of anger… they were alone, maybe now she could talk to him.

"Did I say that?" He lowered his eyes looking straight into hers. He wasn't happy.

"You make it impossible for anyone to be nice to you, you know that?" Rory bit out before she could stop herself, she was trying to steer the conversation somewhere else. She needed to tell him that she had changed her mind about the dare.

"Gee, I really wish we could continue your analysis on how pathetic I am," Tristan stepped forward making Rory take a step back. He leaned down and reached into her book bag. Rory's heart fell through her stomach when Tristan pulled out the paperback, held it in front of her face for a second so that she could understand the meaning behind his actions, and stuffed it into his back pocket, "unfortunately, I have to meet some friends"

Rory's heart ached as he pushed past her and out the studio.

"Where are you going?" Paris frowned "Where is he going? We're not finished! Hey, I'm the director here! Tristan!"

"Tristan," Brad's face blanched, "come back!"

Rory felt ill, she felt faint, she had to go.

"Hey!" Paris called angrily, "Where are _you_ going now?!"

Rory raced outside in time to catch Tristan right before he got in his car,

"Tristan!"

"No more Rory"

"The game?" Rory wanted to crumble

"No, this… you and me, no more. I need a break" Tristan's resolute tone felt like a hundred doors slamming in her face.

"For how long?" Rory's voice cracked

"I don't know…" Tristan ran his hand through his hair mulling that over, "probably until after Chilton"

"You can't be serious" Rory felt her heart break

"I am" Tristan looked down to meet her eyes. He pulled the paperback back out, "I dare you"

"I… I can't do that" Rory felt like crying. She was grateful that it was already dark out so he wouldn't see.

"Don't worry" Tristan breathed in deeply resolved to go through with what he had in mind, "I'll make it easy for you"

Tristan backed away from Rory and got in his car taking off before he changed his mind.

"Tristan?" Rory breathed out heart broken and confused.

****End of Part 12****

 

**Notes for the Chapter:**

> A/N - Aww.. this one broke my heart. I was quickly running out of episodes with Tristan in them, so the story had to wind down. Up until this point I had so much fun writing this, mixing in my story with canon. Hope you liked it too. One more part to go. 
> 
>  


	13. Chapter 13

****Part 13****

Opening night was full of tension and dread, for Rory, the night was particularly edgy… she hadn't seen Tristan since the night before.

"He's not here" Paris found her on the hall

"Who's not here?"

"Tristan" Paris confirmed what Rory had felt when she entered the building, "I've looked everywhere. I called his home, his cell, I called three girls I know he's seeing"

"Paris, calm down" Rory ignored her last comment

"Weren't you listening?" Paris was not calming down, "He's not here. We're on in twenty minutes and we don't have a Romeo. We are going to fail"

"We're not going to fail" _we're going to fail…_ Rory thought

"Do you think Harvard accepts people who fail Shakespeare?" Paris was loosing it, "They don't. I don't have the numbers on it or anything, but I feel pretty secure in saying, you fail Shakespeare, you don't get into Harvard"

"Okay, maybe he's just in one of the bathrooms smoking" Rory needed to get rid of Paris so she could have her own panic attack

"Good idea" Paris took the bait, "you check the east men's rooms, I'll check the west ones"

Rory walked away in hurried steps, she was pretty sure she would not come any closer to finding Tristan than Paris would, but she couldn't stand around not doing anything. She went to look for his car, she knew what it looked like, but it wasn't in the parking lot or anywhere around Ms. Patty's studio. She wanted to call his phone but she didn't have his number, she wanted to call out his name, but that was obviously a ridiculous idea. Resigned to the fact that she was no better at finding him than Paris had been, Rory went back inside. Paris pounced on her almost immediately,

"I knew he was going to do this, but no one wanted to listen to me. It was all, let's make Tristan Romeo, he's hot"

"What about Brad?" Rory asked softly

"Brad transferred schools" Paris brushed off impatiently. She was right about to go into another tirade when Tristan appeared around the bend detached and aloof.

"Where have you been?" Paris attacked, "you have to get dressed, we're on in ten minutes"

"Can't" Tristan blurted out

"What?"

"Actually," Tristan tried, "my dad had me pulled out of school. He…"

Paris, tired, frustrated, and obviously still in need of a Romeo had no time to hear excuses and walked away.

"…and is she unhappy" Tristan noted

"What do you mean he had you pulled out of school?" Rory asked him worried suddenly, "What happened?"

"Nothing. Just ticked the old man off, that's all"

"By doing what?" Rory tried to meet his eyes, "Tristan, come on, tell me"

"I got in some trouble"

"Trouble involving?" Rory furrowed her brow

"Involving Duncan and Bowman, and Bowman's dad's safe" Tristan lowered his voice at the last part.

"Oh no" Rory breathed out

"I mean, Bowman had a key. It was supposed to be no big deal," Tristan shrugged his shoulders, "and the crazy silent alarm kicked in"

"You broke into Bowman's dad's safe?"

"Yes" Tristan said calmly

"Stupid" Rory pouted angrily

"Yes" Tristan repeated

"Well, okay" Rory rationalized, "you can apologize and you can put back the money and you can explain that, I don't know, you were going through something"

"I was," Tristan kept his voice monotone, "I was going through his safe"

"Why would you do this?" She really didn't want him to answer that.

"To give you a shot at completing the dare I guess… I don't know" he answered with a slight air of sarcasm, "I guess that's something I can ponder at military school"

"Military school?"

"The police are letting our parents handle it, and in my case that means military school in North Carolina"

"I don't know what to say" but she did, she had a million things to say, she just couldn't pick where to start.

"Well, I imagine you're overwhelmed with the relief in knowing that soon I will be gone, dare's all but handed to you"

"I'm not; this is not what I wanted" Rory scrambled to find something appropriate to say, "I'm so sorry; I don't want you to go"

"Well, I have to. I'm a big boy. I can handle it"

"There's nothing you can't…" Rory started feeling an anguish she didn't know possible; she wanted to tell him she was sorry. She wanted to take back her dare but at that moment Tristan's father appeared around the bend and called his son. Tristan flinched,

"I gotta go" Tristan said softly. He wasn't so angry with Rory anymore… and he wished he hadn't gone through that stupid dare… but there was no sense in crying over spilt milk. Tristan leaned in closer so that Rory had to look up to see his eyes, her chest stopped moving as she held her breath, "So, I might kiss you goodbye but, uh… your boyfriend's watching. Take care of yourself, Mary"

Tristan turned around then disappearing into the hallway, hands in his pocket, clearly crestfallen. Rory knew Dean was standing behind her, and breathed in deeply willing the tears in her eyes to dry up.

"What are you standing there for?" Paris barged in dressed as Romeo, "Let's go. You better start sucking on an Altoid"

*** * END * ***

**Notes for the Chapter:**

> A/N - Part of writing is taking risks. Taking a plot line where you didn't think you would take it and make something worthwhile out of it. Writing this fic was definitely that for me. I never got to chat with the person who requested it or even know if they liked it, but if I could thank them for requesting it I totally would. I hope you enjoyed reading it. I most certainly enjoyed writing it.   
>  \--Rd


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